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Jason Scott graduated from Horace Greeley High School in Chappaqua, New York and served on the staff of the school newspaper under the title "Humor Staff". While in high school he produced the humor magazine Esnesnon ("nonsense" backwards).[3] He later earned a degree in Mass Communications (Concentration in Film) from Emerson College in Boston, Massachusetts. While at Emerson, he worked for the school humor magazine, school newspaper, WERS 88.9 FM radio, and served as art director on several dramatic plays.

In 1990, along with John Anthony Rescigno (who was known by the pseudonym "Trout.Complex"), Sadofsky started TinyTIM, a popular MUSH. He resigned in 2000.[5] In 1995, Jason joined the video game company Psygnosis as a technical support worker, before being hired by a video game startup, Focus Studios, as an art director. After Focus Studios' closure, Jason moved into UNIX administration,[6] where he remained until 2009.

In 2006 he announced starting a documentary on Arcades, titled ARCADE, but it is currently on hold while GET LAMP is being worked on.[8]

In 2007, he co-founded Blockparty, a North American demoparty. For their inaugural year, they paired up with Notacon which takes place annually in Cleveland, Ohio. This collaborative effort allowed the fledgling party to utilize the existing support structure of an established conference. In January 2009, he formed "Archive Team",[9] a group dedicated to preserving the historical record of websites that close down. Responding[10] to the announcement by AOL of the closure of AOL Hometown, the team has also announced[11] plans to save[12] Podango and GeoCities.

In October 2009, he started raising funds for a year-long sabbatical from his job as a computer systems administrator, to pursue technology history and archival projects full-time. By November 2009, he had reached his funding goals, with the support of over 300 patrons.[13]